4-(2-Oxa-6-azaspiro[3.3]heptan-6-ylmethyl)-2-chlorophenol → (3-(4-(2-Oxa-6-azaspiro[3.3]heptan-6-ylmethyl)-2-chlorophenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

HRID 1639513Notes

Reaction equation

HRID 1639513 reaction equation
[CH2:1]1[C:4]2([CH2:7][N:6]([CH2:8][C:9]3[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([Cl:16])[CH:10]=3)[CH2:5]2)[CH2:3][O:2]1.CC1C=CC(S(O[CH:28]2[CH2:31][N:30]([C:32]([C:34]3[O:35][C:36]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[N:37][N:38]=3)=[O:33])[CH2:29]2)(=O)=O)=CC=1>>[CH2:3]1[C:4]2([CH2:5][N:6]([CH2:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH:28]4[CH2:29][N:30]([C:32]([C:34]5[O:35][C:36]([C:39]6[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=6)=[N:37][N:38]=5)=[O:33])[CH2:31]4)=[C:11]([Cl:16])[CH:10]=3)[CH2:7]2)[CH2:1][O:2]1

Participants

3

Reactant 2

HCID 595635084-(2-Oxa-6-azaspiro[3.3]heptan-6-ylmethyl)-2-chlorophenolHCID 59563509HCID 59563509, compound

Product 1

HCID 49802133(3-(4-(2-Oxa-6-azaspiro[3.3]heptan-6-ylmethyl)-2-chlorophenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanoneYield 51.6%

Procedure

Using a similar protocol as described in Example 2 but employing 8A (130 mg, 0.54 mmol) and 8B (220 mg, 0.55 mmol) as starting materials afforded 130 mg (51%) of 8 as a gum. 1H NMR (500 MHz, CD3OD): δ 3.38 (s, 4H), 3.48 (s, 2H), 4.25 (dd, 1H), 4.6-4.8 (m, 6H), 5.15 (m, 2H), 6.78 (d, 1H), 7.15 (d, 1H), 7.32 (s, 1H), 7.56 (t, 2H), 7.61 (t, 1H), 8.09 (d, 2H), MS (APCI+) m/z 467 [M+H]+, LC purity: 91%.

Sources & evidence

ORD record
ord-701d5c5f91014782a137a564f32574f8
Source dataset
uspto-grants-2012_02
Patent number
US08110566B2

Reaction notes

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